Simon’s Tavern

Steeped in Chicago history, the original 1930s mahogany bars and back bars are still the focal points at this Andersonville hangout. The owner became a bootlegger during Prohibition, and cashed people’s paychecks while sitting in a bullet-proof booth, which is still there. Mosaic tables dot the space, which is surrounded with wood paneling. A mural, painted in the 1940s, depicts the owner and his friends partying after a deer hunt. After the death of the original owner, his son owned the bar until 1994. If you ask, the current owner may even take you on a tour